CN101883563B - Injection comprising docetaxel and its preparation - Google Patents
Injection comprising docetaxel and its preparation Download PDFInfo
- Publication number
- CN101883563B CN101883563B CN200780101762.9A CN200780101762A CN101883563B CN 101883563 B CN101883563 B CN 101883563B CN 200780101762 A CN200780101762 A CN 200780101762A CN 101883563 B CN101883563 B CN 101883563B
- Authority
- CN
- China
- Prior art keywords
- injection
- docetaxel
- mother solution
- ethanol
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention provides an injection comprising docetaxel, which contains a mother liquid, ethanol for preventing gel formation of injection, water for keeping the mother liquid in a uniformly flowing state. The mother liquid is a solution containing docetaxel and one or more pharmaceutically acceptable surfactants. The invention also provides a process for preparing the injection consisting of mixing the mother liquid with ethanol, then adding water and mixing uniformly. The injection has high uniformity and high stability, and can extend the time needed to form a crystal precipitation of docetaxel in the injectable solution.
Description
Technical field
The invention provides a kind of injection containing docetaxel, especially be a kind of injection containing docetaxel that extends stability and facilitate healthcare givers to use, this injection is the injection containing docetaxel that comprises three components.
Background technology
Belong to the Paclitaxel (Paclitaxel) of taxanes (taxane) checking and approving through united states drug control food office (FDA) in 1992, and become PTS, be considered to past one of most important cancer therapy drug for over ten years, but the initial stage of this medicine listing is not smooth, except raw material is as limited in the source such as Pacific yew and Ramulus et folium taxi cuspidatae, in the time of first stage (first phase) human trial, there is serious anaphylaxis in the patient that this Paclitaxel treatment is accepted in discovery, and anaphylactogen is not Paclitaxel, but be used for dissolving the solvent C remophor EL of Paclitaxel, the anaphylaxis that allows patient produce in order to solve Cremophor EL, the solvent of looking for alternative Cremophor EL is the direction of studying at present.
Because the repellency (hydrophobicity) of taxanes is high, the dissolubility of water is less than to 10 μ g/mL, so it is not smooth with the solvent of dissolving Paclitaxel to look for alternative Cremophor EL, unique Paclitaxel Department of Pharmacy checking and approving is by the intravenous injection of Shi Guibao company of U.S. research and development at present
but it is still to use ethanol and Cremophor EL to mix with 1: 1 ratio that this intravenous injection is used for dissolving the solvent of Paclitaxel, though the reduction of the content of Cremophor EL, but still can cause patient's anaphylaxis.
Although also there is research worker to propose to substitute Cremophor EL to dissolve Paclitaxel (Andersson, B, " Parenteral Paclitaxel in a Stable Non-toxic Formulation " with organic solvent, USP5,877,205, March 2,1999; Hausheer, F.H., Murali, D., and, Seetharamulu, P., USP6,040,330, " Pharmaceutical Formulations of Taxanes ", March 21,2000), its disclosed preparation technology is simple and easy, has very much the market advantage, but these organic solvents have toxicity, therefore do not adopted widely.
Current many research worker, in order to look for alternative solvent, are just carried out towards two aspects:
1. the formula of improvement injection:
It mainly dissolves Paclitaxel with micro-fat body dosage form and Emulsion, but, micro-fat body dosage form can produce precipitation between the storage life, make this stability of drug products deficiency, so store with the state that freezes crystalline flour end while storage, but dry micro-fat body dosage form gelation crystalline flour end must, through expensive freeze-drying preparation technology, therefore to not met to economic benefit, make product lose business-like meaning.
And the research of Emulsion is at Panagyiotis, P. wait people, Kaufman, R.J. wait people and Chu, I.M. in the periodical that waits people to deliver, have (the Panayiotis that discloses, P.et al, WO02/26208, " Emulsion Vehicle for Poorly Soluble Drugs ", April 4,2002; Kaufman, R.J., and Richard, T.J., USP5,616,330, " Stable Oil-In-Water Emulsions Incorporating a Taxine (Taxol) and Method of Making Same ", April 1,1997; Chu, I.M., and Wang, T.R., USP6,348,491, " Oil-In-Water Emulsion for Encapsulation Paclitaxel ", Feb.19,2002), and the existing goodish effect of the Paclitaxel Emulsion made from Emulsion, but the process of its making is complicated, with high costs, and the same with micro-fat body dosage form, between the storage life, can produce crystalline deposit, therefore the stability deficiency of this medicine.
2. synthesize the Docetaxel (docetaxel) of dissolubility higher than Paclitaxel:
Because taxanes is extremely low to the dissolubility of water, and extremely difficulty searches out good solvent, therefore synthesizes dissolubility compared with the much higher alkene paclitaxel of Paclitaxel, the Docetaxel intravenous formulations that this Docetaxel is made with chemical synthesis
go on the market by checking and approving of U.S. FDA, said preparation is with surfactant dissolves, and it is sizable breakthrough in this research field at present.
But, replace Cremophor EL to dissolve in the research of Docetaxel or some shortcoming with surfactant, although this surfactant adopts tween (Tween), it can reduce used the toxicity of organic solvent as solvent in the past, but when injecting while dissolving the medicament of Docetaxel with Tween, this medicament and infusion liquid must be mixed as 5% G/W, but now this mixed liquor can be because thickness and form gel too, must be through just solubilized of violent stirring, in order to improve said circumstances, the grand Borland Luo Er of method business company (Rhone-Poulenc) proposes to add two component compositionss of intermediate solution, avoid by this generation (the precious Mike Bobi of gel, handkerchief Cui Ke Delandi, Ji Lisi chief is auspicious, John Cameron Mitchell Villard, " two component injection compositionss of the additive when containing the Taxane derivative in surfactant and preventing dilution ", No. 00271395th, TaiWan, China patent of invention notification number), this intermediate solution comprises that molecular weight is lower than 200 the additive such as organic compound or sodium chloride and water, this intermediate solution is the aqueous solution of this additive, the large 6wt% of its concentration ratio surfactant, in claims of this Patent Case, the concentration of this intermediate solution is the ethanol that thin up becomes 13wt%, but, after adding this intermediate solution, can produce following problem:
(a) use problem: according to the suggestion of the 27th edition General Chapters<1151>pharmaceutical dosage forms-injections of American Pharmacopeia, need to be at when injection filling excess volume (excess volume) in injection tube for general viscous fluid, the injection consumption of for example 0.5ml, need the excess volume of extra filling 0.12ml (24wt%), because the viscosity of the injection that contains Docetaxel and surfactant is higher, the excess volume of required interpolation also can improve, therefore cause the increase of cost, and healthcare givers need to spend long time to draw the injection of this thickness, and cannot grasp the dose of actual absorption, and then affect precision and the curative effect of patient's medication, although the intermediate solution adding contributes to reduce the viscosity of injection, but reduction degree is limited, so still there will be the problems referred to above.
(b) prepare risk: due to the intermediate solution ethanol that is 13wt%, but commercially available ethanol is generally 95%, therefore 95% ethanol must pass through weighing, go out again the ethanol of 13wt% with water mixing preparation, but, everyone may have a little difference by each redeployed ethanol, and for the sake of security, must pass through again the step of sterilizing, so the complexity in the manufacturing and risk significantly improve especially, use comparatively speaking commercially available 95% ethanol more to simplify and produce and reduce aseptic manufacture risk, progressive is apparent especially.
Stability problem: the medicament of allocating cannot be in stable state for a long time, and the description of this method business dragon Borland Luo Er product that company goes out just emphasizes that this product must use in 4 hours, and according to experimental results show that this product will produce crystalline deposit greatly in 12 hours, this crystallization meeting artery-clogging, therefore can allow patient be absorbed in fatal danger.
Summary of the invention
The inventor is because above-mentioned dissolving Docetaxel intravenous formulations
solvent be still and cannot make said preparation have good stability, therefore invent this three component injection agent containing docetaxel.
The object of the present invention is to provide a kind of three component injection agent containing docetaxel that extend stability and facilitate healthcare givers to use.
For reaching above-mentioned purpose, the present invention comprises containing three component injection agent of docetaxel:
Mother solution, it is the solution that contains Docetaxel and medical acceptable surfactant;
Ethanol, it is the anti-gelation agent in order to prevent from forming after injection from mixing gel;
Water, it is in order to coordinate the flowable that makes aforementioned mother solution be even shape with aforementioned ethanol.
Wherein the weight of anti-gelation agent compared with surfactant weight ratio for being not less than one of percentage; The weight of flowable compared with surfactant weight ratio for being not less than 10.
The present invention can avoid mother solution to mix the gel being produced with infusion liquid as 5% G/W in the time using by adding anti-gelation agent, and flowable can coordinate anti-gelation agent to adjust the viscosity of mother solution, therefore by compound method of the present invention the reduced viscosity of redeployed three component injection agent, and make it reach uniform state (homogeneous), and can not produce gel, facilitate healthcare givers to draw this injection with syringe, and confirm extraction amount, in addition, can also extend the time that Docetaxel produces crystalline deposit from the solution of injection, therefore increase the stability of injection, the fatal risk being produced during with reduction patient medication, improve by this quality of medical care.
Injection containing docetaxel of the present invention, wherein, the acceptable surfactant of described medicine is preferably tween.Wherein, the concentration of the ethanol adopting is preferably not less than 90%, is more preferably not less than 95%; In described mother solution, the concentration of Docetaxel is preferably 20mg/ml to 60mg/ml; The weight of described anti-gelation agent ethanol is preferably at least 1% of tween weight; The weight of described water is preferably at least 10% of tween weight.
The present invention also provides a kind of method of preparing the injection containing docetaxel claimed in claim 1, and its step comprises: a) mother solution and ethanol are mixed into mixed liquor; B) water is added in above-mentioned mixed liquor, and mix homogeneously.
Accompanying drawing explanation
Fig. 1: the schematic top plan view of circular injection bottle when uniformity test of the present invention.
Specific embodiments
Describe the present invention in detail below in conjunction with accompanying drawing, but do not limit practical range of the present invention.
The present invention is containing the injection of docetaxel, and it comprises:
Mother solution, it contains Docetaxel and one or more pharmaceutically acceptable surfactant solutions, this surfactant is tween (tween, be Polysorbate), and the concentration that this Docetaxel is dissolved in tween is that 20 mg/ml (mg/ml) are to 60 mg/ml (mg/ml);
Anti-gelation agent, it act as can avoid mother solution to mix the gel being produced with infusion liquid as 5% G/W in use, this anti-gelation agent is preferably 95% ethanol, and its weight is not less than one of percentage of tween weight (tween of ethanol >=1wt%);
Flowable, it is for to coordinate with anti-gelation agent so that mother solution is the water of even shape, and its effect is the viscosity of capable of regulating mother solution, and this flowable is pure water or water for injection, and its weight is not less than 10 (tween of water >=10wt%) of tween weight.
The three component injection agent that this anti-gelation agent, flowable and mother solution form more can be allocated flexibly, and flexibly adjust the viscosity of mother solution compared with the combination of intermediate solution of the prior art and mother solution.
The compound method of the three component injection agent containing docetaxel of the present invention, it is after mother solution is mixed homogeneously with anti-gelation agent, then adds flowable mix homogeneously.
Above-mentioned compound method is in the time that need use, directly, at room temperature in hand mode or as auxiliary modes of machine such as desktop nest stream machines (Vortex), to allow each component reach even in the time mixing.
Set forth below the advantage of the injection containing docetaxel of the present invention with several embodiment:
embodiment mono-observes with different mixing modes the phenomenon that gel produces
The present invention can utilize diverse ways to mix with easy to use, and observes the situation that gel produces.
Matched group:
This group experiment is the same with the intermediate solution of prior art, is first about to this anti-gelation agent mix with flowable, then carries out different blend steps, and the mother solution using, anti-gelation agent and flowable are as table 1, and different mixed methods and observed result thereof are as table 2 and table 3.
Table 1.
Table 2.
Table 3.
Relatively two kinds of methods, the composition of its final mixed solution is identical, but tween molecule part composition is around different, wherein the anti-gelation agent of mixed method 1 and flowable can first be adsorbed on tween molecule, make tween molecule contain more anti-gel molecule around, the local concentration (local concentration) that is the anti-gelation agent of surfactant molecule is higher, therefore can avoid the generation of gel; And in mixed method 2, in the time that the mother solution that contains tween injects primer solution, this anti-gelation agent and flowable have first been poured solution dilution, cause tween molecule anti-gel molecular concentration around too low, thereby make to produce in overall solution the gelatin phenomenon of varying degree.
The main cause that the consumption of anti-gelation agent that hence one can see that not avoids gel to produce, its main cause is to depend on whether anti-gelation agent can fill part and mix homogeneously with the surfactant molecule in mother solution in the process of mixing, and just can avoid by this and other surfactant molecule generation coagulation.
Experimental group:
Mother solution, anti-gelation agent and flowable that this group is used are as table 4, but blend step is different from matched group, and it is that anti-gelation agent is mixed with mother solution respectively with flowable, and its blend step and observed result be as table 5, and make comparisons with matched group.
Table 4.
Table 5.
The present embodiment sequentially drops into mother solution by anti-gelation agent and flowable and (is different from mixed method 2, to drop into mother solution with anti-gelation agent and flowable institute mixed liquor), through observing, anti-gelation agent molecule has higher concentration around in surfactant molecule, it is 5wt% (< 6wt%) that this mixed method can make the ratio of anti-gelation agent molecule and surfactant molecule, and gel-free produces.
embodiment bis-mobility experiments
Have or not the injection that adds flowable as table 6, and the mixed scenario of observation and more each injection.
Table 6.
Learnt by the present embodiment, in injection, have the flowable of interpolation can reduce solution viscosity, thereby the filling that can reduce excess volume to be to reduce production costs, and it is more convenient to make to draw this injection, and can precisely controls the injected dose of absorption.
embodiment tri-uniformity tests
After each component mixes, pass through different stirrings to make injection, then test its uniformity.
Please refer to shown in Fig. 1, the test of the uniformity is take the top view of circular injection bottle as benchmark, get the sample points that the long-pending central point of its circular radial section and circumference 0 are spent, 90 degree, 180 are spent and 270 degree are the uniformity, analyze with high-performance liquid chromatograph (High Performance Liquid Chromatography).
Matched group:
The experiment of this group is the same with the intermediate solution of prior art, first being about to this anti-gelation agent and flowable is mixed into intermediate solution, after extracting again intermediate solution, slowly inject mother solution, and stir with different alr modes, analyze again, the mother solution, anti-gelation agent and the flowable that use be as table 7, and observed result after stirring is as table 8 and table 9.
The composition of table 7. two component injection agent compositionss
Extract after the intermediate solution of above-mentioned inspection product project 1 and 2, be injected into lentamente in mother solution, carry out at least 40 seconds in the mode of gentle Stirring, this gentleness Stirring is to allow intermediate solution and mother solution not produce bubble in the time stirring again, and the analysis result obtaining is as follows:
The gentle agitation uniformity testing of table 8. two component injection agent compositionss
(concentration unit is mg/ml)
Extract after the intermediate solution of above-mentioned inspection product project 1 and 2, be injected into lentamente in mother solution, with desktop turbine (Vortex) high degree of agitation at least 40 seconds, make the mixing material of intermediate solution and mother solution produce bubble again, the analysis result obtaining is as follows:
The high degree of agitation uniformity testing of table 9. two component injection agent compositionss
(concentration unit is mg/ml)
From above-mentioned analysis result, the injection of the mixability of the injection after high degree of agitation after compared with gentle agitation is even.
Experimental group:
The experiment of this group is injected mother solution by this anti-gelation agent and flowable respectively, and stir with different alr modes, then analyze, the mother solution, anti-gelation agent and the flowable that use are as table 10, and analysis result after stirring is as table 11 and table 12, then make comparisons with matched group.
The composition of table 10. three component injection agent compositionss
The anti-gelation agent that extracts respectively three component injection agent compositionss of above-mentioned inspection product project 3,4,5,6 adds in mother solution, again with desktop turbine (Vortex) high degree of agitation at least 20 seconds, then add respectively again flowable to stir at least 20 seconds in the mode of gentle Stirring, this gentleness Stirring refers to and allows final solution not produce bubble in the time stirring, and the analysis result obtaining is as follows:
The gentle agitation uniformity testing of table 11. three component injection agent compositionss
(concentration unit is mg/ml)
The anti-gelation agent that extracts respectively three component injection agent compositionss of above-mentioned inspection product project 3,4,5,6 adds in mother solution, again with desktop turbine (Vortex) high degree of agitation at least 20 seconds, then add respectively again flowable with desktop turbine (Vortex) high degree of agitation at least 20 seconds, make the mixing material of anti-gelation agent and mother solution produce bubble, the analysis result obtaining is as follows:
The high degree of agitation uniformity testing of table 12. three component injection agent compositionss
(concentration unit is mg/ml)
Local concentration (local concentration) by known this surfactant molecule of embodiment 1 anti-gelation agent is around higher, therefore except can reducing the uniformity resistance that the ratio of gel in solution and gel itself produce; Relative, two component injection agent of matched group are compared to experimental group of the present invention, because the surfactant of two components is diluted in advance, thereby make surfactant molecule anti-gelation agent local concentration (local concentration) around lower, so cannot reduce the resistance that gel ratio and gel itself produces, even after high degree of agitation, the uniformity of its solution still three component injection agent more of the present invention is poor.
embodiment tetra-stability tests
After injection composition is mixed, place at room temperature, observe the situation of different standing times and crystallization.
Matched group:
In extraction table 7, examine after the intermediate solution of product project 1 and 2, be injected in mother solution lentamente, then with desktop turbine (Vortex) high degree of agitation at least 40 seconds, carry out the test of stability, result is as table 13:
The crystallization trial of table 13. two component injection agent compositionss after high degree of agitation
Experimental group:
The anti-gelation agent of three component injection agent compositionss of the inspection product project 3,4,5,6 in extraction table 10 adds in mother solution respectively, again with desktop turbine (Vortex) high degree of agitation at least 20 seconds, then add respectively again flowable with desktop turbine (Vortex) high degree of agitation at least 20 seconds, carry out again afterwards the test of stability, its result is as table 14, and makes comparisons with matched group:
The crystallization trial of table 14. three component injection agent compositionss after high degree of agitation
Higher with the local concentration (local concentration) of known this surfactant molecule of embodiment 3 anti-gelation agent around by embodiment 1, therefore except can reducing the uniformity resistance that the ratio of gel in solution and gel itself produce, but also can improve the energy barrier between this surfactant molecule, avoid Docetaxel molecule to produce crystalline deposit because of intermolecular gathering; Relative, when the surfactant molecule of two component injection agent of matched group anti-gelation agent local concentration (local concentration) around lower, therefore the energy barrier between surfactant molecule is lower, therefore two component injection agent will produce crystalline deposit placing after 12 hours, and three component injection agent of experimental group of the present invention are placing in 48 hours all without generation crystalline deposit.
Adding anti-gelation agent can avoid mother solution in the time using, to mix produced gel with infusion liquid, and flowable can coordinate anti-gelation agent to adjust the viscosity of mother solution, therefore by compound method of the present invention the reduced viscosity of redeployed three component injection agent, and make it reach uniform state (homogeneous), and can not produce gel, facilitate healthcare givers to draw this injection with syringe, and confirm extraction amount, in addition, can also extend the time that Docetaxel produces crystalline deposit from the solution of injection, therefore increase the stability of injection, the fatal risk being produced during with reduction patient medication, improve by this quality of medical care.
Claims (2)
1. containing three component injection agent of docetaxel, it is made up of following three components:
Mother solution, it is the solution that contains Docetaxel and medical acceptable surfactant;
Ethanol, it is the anti-gelation agent in order to prevent from forming after injection from mixing gel;
Water, it is in order to coordinate the flowable that makes aforementioned mother solution be even shape with aforementioned ethanol;
And it is wherein a kind of that the consumption of described mother solution, ethanol and water is selected from following composition:
After wherein in use described mother solution being mixed homogeneously with ethanol, then add water mix homogeneously, wherein, the acceptable surfactant of described medicine is tween, and in described mother solution, the concentration of Docetaxel is 20mg/ml to 60mg/ml.
2. a method of preparing the three component injection agent containing docetaxel claimed in claim 1, its step comprises:
A) mother solution and ethanol are mixed into mixed liquor; And
B) water is added in above-mentioned mixed liquor, and mix homogeneously.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2007/071274 WO2009079878A1 (en) | 2007-12-19 | 2007-12-19 | Injection comprising docetaxel and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101883563A CN101883563A (en) | 2010-11-10 |
| CN101883563B true CN101883563B (en) | 2014-07-09 |
Family
ID=40800697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200780101762.9A Active CN101883563B (en) | 2007-12-19 | 2007-12-19 | Injection comprising docetaxel and its preparation |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP2011506495A (en) |
| KR (1) | KR20100113527A (en) |
| CN (1) | CN101883563B (en) |
| WO (1) | WO2009079878A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101862319B (en) * | 2010-06-28 | 2012-01-11 | 江苏奥赛康药业股份有限公司 | Docetaxel combination for injection and preparation method thereof |
| JP6124633B2 (en) * | 2013-03-18 | 2017-05-10 | ダイト株式会社 | Stable docetaxel injection |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5750561A (en) * | 1991-07-08 | 1998-05-12 | Rhone-Poulenc Rorer, S.A. | Compositions containing taxane derivatives |
| WO2007124700A2 (en) * | 2006-05-03 | 2007-11-08 | I.Q.A., A.S. | Pharmaceutical composition containing taxane derivative destined for the preparation of an infusion solution, method of preparation thereof and use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005225818A (en) * | 2004-02-13 | 2005-08-25 | Otsuka Pharmaceut Factory Inc | Medicinal composition of paclitaxel or docetaxel |
-
2007
- 2007-12-19 KR KR1020107016036A patent/KR20100113527A/en not_active Application Discontinuation
- 2007-12-19 WO PCT/CN2007/071274 patent/WO2009079878A1/en active Application Filing
- 2007-12-19 CN CN200780101762.9A patent/CN101883563B/en active Active
- 2007-12-19 JP JP2010538312A patent/JP2011506495A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5750561A (en) * | 1991-07-08 | 1998-05-12 | Rhone-Poulenc Rorer, S.A. | Compositions containing taxane derivatives |
| WO2007124700A2 (en) * | 2006-05-03 | 2007-11-08 | I.Q.A., A.S. | Pharmaceutical composition containing taxane derivative destined for the preparation of an infusion solution, method of preparation thereof and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20100113527A (en) | 2010-10-21 |
| CN101883563A (en) | 2010-11-10 |
| WO2009079878A1 (en) | 2009-07-02 |
| JP2011506495A (en) | 2011-03-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2016258642B2 (en) | Cabazitaxel fat emulsion injection, and preparation method and use thereof | |
| CN107149592B (en) | Biological self-assembly nano-crystalline injection and preparation method with lympha targeted function | |
| CN101606934A (en) | Bendamustine hydrochloride compound | |
| CN103705442B (en) | Lipid gel pharmaceutical preparation in situ and its production and use | |
| CN101883563B (en) | Injection comprising docetaxel and its preparation | |
| WO2007009355A1 (en) | Paclitaxel injection and preparation method thereof | |
| CN101264063A (en) | Stable tetrodotoxin preparations under room temperature for injection | |
| CN101721370A (en) | Goserelin release microsphere preparation, preparation method and detecting method thereof | |
| CN104822369A (en) | Compositions comprising spicamycin derivatives and methods of use thereof | |
| CN101244259B (en) | Thymus gland peptide alpha1sustained-release microsphere preparation for injection and preparation thereof | |
| CN104095815B (en) | The preparation method of the emulsifiable injection of Tulathromycin | |
| CN101190213A (en) | Docetaxel injection and preparation method thereof | |
| CN107898757A (en) | A kind of carrier medicament and preparation method thereof | |
| CN109528632A (en) | Nimodipine pharmaceutical composition, nimotop vial and preparation method thereof | |
| TWI321471B (en) | Three-part injectable composition comprising docetaxel in a surface active agent and an additive to prevent gelling on dilution and diluent | |
| CN102793678B (en) | A kind of preparation method of the Docetaxel injection without tween | |
| CN105816424B (en) | A kind of argatroban composition and preparation method thereof | |
| CN107427486A (en) | Pharmaceutical composition, manufacture method and application method containing taxane cyclodextrin compound | |
| CN107789324A (en) | A kind of injection De Lasha star meglumines and preparation method thereof | |
| CN102793663B (en) | Sustained-release microsphere injection containing antitumor drug (2-methoxyestradiol) | |
| CN111603439A (en) | Long-acting in-situ phase change gel injection of brexpiprazole and preparation method thereof | |
| CN101327206A (en) | Docetaxel injection and preparation method thereof | |
| CN103536529A (en) | Ceftiofur-containing long-acting injection and preparation method | |
| CN104644548B (en) | Lecithin is as taxol and its combination of derivative injection medicine and application | |
| CN108066335A (en) | A kind of pharmaceutical composition containing taxol or its analog and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: DE Ref document number: 1144151 Country of ref document: HK |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| ASS | Succession or assignment of patent right |
Owner name: TOT BIOPHARM CO., LTD. Free format text: FORMER OWNER: TTY BIOPHARM CO., LTD. Effective date: 20141008 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: TAIWAN, CHINA TO: 215024 SUZHOU, JIANGSU PROVINCE |
|
| TR01 | Transfer of patent right |
Effective date of registration: 20141008 Address after: 215024 No. 120, Changyang street, Suzhou Industrial Park, Jiangsu Patentee after: TOT BIOPHARM COMPANY LIMITED Address before: Taiwan, Taipei, China three East Road, No. 170, 4 floor Patentee before: China Taiwan Dongyang pharmaceutical industry Limited by Share Ltd |
|
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: WD Ref document number: 1144151 Country of ref document: HK |